- Synthesis and Optoelectronic Properties of Thiophene Donor and Thiazole Acceptor Based Blue Fluorescent Conjugated Oligomers
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We report on the synthesis and characterization of low band gap, blue light emitting and thermal stable conjugated oligomer by Wittig condensation. Thiophene and thiazole type of donor-acceptor based series of conjugated oligomers, Oligo-4,5-bis-[2-[5-[2-thiophene-2-yl-vinyl]thiophene-2-yl]-vinyl]-thiazole (OBTV-TZ) and Oligo-2,4,5-Tris–[2-[5-[2-thiophene-2-yl-vinyl]thiophene-2-yl]-vinyl]-thiazole (OTTV-TZ) were synthesized. These oligomers were confirmed by FT-IR and 1H-NMR and LC/MS analysis. The effect of the number of thiophene rings on the optical, electrochemical, thermal and morphological properties of the oligomers were systematically investigated. Both oligomers were exhibited almost same absorption wavelength in methanol solution (λmax?=?365?nm and 369?nm) which indicates both oligomers illustrate similar intra molecular charge transfer (ICT). In solid state, the oligomers were exhibited broadening peaks with higher onset absorptions (λmax?=?600?nm and 580?nm). The photoluminescence absorption spectrum of the oligomers was observed at 433?nm and 434?nm respectively in methanol solution with blue emission. The electrochemical band gap (Egec) of the OBTV-TZ was 1.55?eV (low band gap) and OTTV-TZ was exhibited greater highest occupied molecular orbital (HOMO) value (EHOMO?=??6.6?eV). Moreover morphological parameters of both oligomer film of 2D and 3D diagrams were observed by using AFM studies.
- Mahesh,Karpagam
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- Dialkylfluorene-oligothiophene and dialkylfluorene-dithienylvinylene alternating copolymers
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Well defined dialkylfluorene/oligothiophene and dialkylfluorene/dithienylvinylene alternating copolymers have been synthesized via the polycondensation of 2,7-dibromo-(9,9-dialkyl-fluorene) with the appropriate distannylated (oligo)thienylene component according to a Stille-type coupling reaction using tetrakis(triphenylphosphine)palladium [Pd(PPh3)4] as catalyst. The alternate incorporation of the thienylene building blocks leads to the tunability of the photoluminescent properties of the alternating copolymers. The long wavelength absorption and photoluminescence maxima of the copolymers display a subsequent bathochromic shift upon increasing the size of the (oligo)thienylene building block.
- Asawapirom,Güntner,Forster,Farrell,Scherf
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- New amidino-benzimidazolyl thiophenes: Synthesis and photochemical synthesis
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The photochemical synthesis of amidino-benzimidazolyl thiophenes was discussed. The amidino-benzimidazolyl-substituted bis-1,2-(2-thienyl) ethenes and benzo[1,2-b:4,3-b′] dithiophenes were prepared by the condensation of amidino-substituted o-phenylene diamines with corresponding dialdehydes. The synthesized bis-cationic bis-amidino benzimidazolyl substituted diphenylfurans were found to inhibit HIV-1 infection.
- Starcevic, Kristina,Boykin, David W.,Karminski-Zamola, Grace
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- Role of cyano substituents on thiophene vinylene benzothiadiazole conjugated polymers and application as hole transporting materials in perovskite solar cells
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Two narrow-band gap of donor-acceptor based conjugated polymers, BTTP and BTTP-CN were synthesized by Wittig copolymerization with thiophene or cyano-vinylene thiophene as the donor and 2,1,3-benzothiadiazole as acceptor units. The polymers were investigated by FT-IR, UV-V is, fluorescence spectroscopy, thermal stability and cyclic voltammetry (CV). The thermal analysis revealed that the BTTP polymer was stable up to 220 °C and BTTP-CN was stable up to 254 °C. The absorption spectra showed absorption maxima at 403 nm for BTTP and 397 nm for BTTP-CN. The polymers BTTP exhibited orange colour fluorescence emission at 585 nm and BTTP-CN exhibited yellow color fluorescence emission at 520 nm. The optical band gap values of undoped polymers BTTP and BTTP-CN were calculated as 2.2 and 2.13 eV respectively. Novel synthesized polymers were then enforced as dopant/additive-free hole transport materials in perovskite solar cells. Both polymers has shown the photovoltaic performance of 3.80 % for BTTP and 3.48 % for BTTP-CN under 1 sun illumination. The photovoltaic performance are compared with reference hole transporting material of spiro-OMeTAD with and without additive as 12.53 and 7.55% respectively.
- Mahesh,Karpagam,Putnin, Thitirat,Le, Huong,Bui, Thanh-Tuan,Ounnunkad, Kontad,Goubard, Fabrice
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- Unusual titanium-induced McMurry coupling of 4-oxo-4H-chromene-2-carbaldehydes enroute to bis-chromones
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Ti/Zn-mediated McMurry coupling of a series of 4-oxo-4H-chromene-2-carbaldehydes afforded unusual chemoselective CH2-CH2tethered bis-chromones. Studying the reaction parameters and reagents further confirmed that the formation of unexpected coupled products is selective to 4-oxo-4H-chromene-2-carbaldehydes. This methodology demonstrated a simple and efficient route for the synthesis of bis-chromones.
- Yerrabelly, Jayaprakash Rao,Bathini, Pavan Kumar,Yerrabelly, Hemasri,Vadapalli, Kishore
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p. 4705 - 4709
(2021/03/22)
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- Synthesis method of diarylethene
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The invention discloses a synthetic method of diarylethene. The method comprise the following steps: potassium acetate and ultrapure water are added to a dry anaerobic tube, and stirred to be dissolved; then re-steamed N,N-dimethylformamide is added, and nitrogen is introduced for deoxygenation; reactants aryl bromide and 1,3-divinyl-1,1,3,3-tetramethyldisiloxane, catalyst palladium acetate, ligand tri-o-tolylphosphine and additive tetrabutylammonium bromide are added sequentially, nitrogen is introduced for deoxygenation, temperature is increased to 100 DEG C, and stirring is performed untila reaction is finished; diarylethene with yield as high as 90% or higher is obtained finally through a post-processing procedure. With adoption of the synthetic method of diarylethene, yield is high,ethylene gas and a pressure container not easy to operate are not needed, and the synthetic method can be widely applied to industrial production and has better market application prospect.
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Paragraph 0049-0051
(2020/09/09)
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- Synthetic method A-D-A configuration organic conjugated micromolecule
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The invention provides a synthesis method of A-D-A conjugated small molecules. The method comprises the following steps: (1) by using 2-formylthiophene as a raw material and using zinc powder and titanium tetrachloride as catalysts, preparing a compound (I); (2) activating the site 2 of the compound (I) by using n-butyllithium, so as to form a lithium salt intermediate; then, adding 1-bromooctane to prepare a compound (II); (3) activating the site 2 of the compound (II) by using n-butyllithium, so as to form a lithium salt intermediate; then, adding trimethyltin chloride to prepare a compound (III); (4) performing reaction by 4,7-dibromo diazosulfide and the compound (III) to prepare a compound (IV); (5) respectively connecting 2-octyl trans-terthienyl based on diazosulfide onto the two ends of R1, R2, R3 and R4 to synthesize final products of S1, S2, S3 and S4.
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Paragraph 0026; 0033-0037
(2019/09/18)
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- Conjugated Oligothiophene Derivatives Based on Bithiophene with Unsaturated Bonds as Building Blocks for Solution-Processed Bulk Heterojunction Organic Solar Cells
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A new building block ATVTA that uses stiff carbon–carbon triple bonds (A) on 1,2-di(2-thienyl)-ethene (TVT) has been developed. Oligothiophene derivatives S-01 with a TVT unit, S-02 with a 5,5′-diethynyl-2,2′-dithienyl (AT2) unit and S-03 with ATVTA were synthesized to compare their effects in a systematic study. Due to the better π-conjugation extension of the TVT unit, S-01 exhibits the most red-shifted absorption profile among them, whereas S-02 possesses the deepest HOMO level. While the HOMO level of S-03 is down-shifted by 0.02 eV relative to that of S-01, the alkyne linkages can effectively down-shift the HOMO level. By replacing the terminal units of S-03 with stronger electron acceptors, S-04 and S-05 exhibited broader absorption profiles and lower HOMO levels than those of S-03. Organic solar cells based on these molecules were fabricated and an S-03:PC60BM (1:1, w/w) based device afforded the highest Voc value of 0.96 V and a power conversion efficiency (PCE) of 2.19 %.
- Cui, Chaohua,Wu, Yue,Cheung, Man-Sing,Ho, Cheuk-Lam,Dong, Qingchen,Lin, Zhenyang,Li, Yongfang,Wong, Wai-Yeung
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p. 3557 - 3567
(2016/12/26)
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- Selective rhodium-catalyzed hydroformylation of alkynes to α,β-unsaturated aldehydes with a tetraphosphoramidite ligand
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A tetraphosphoramidite ligand was successfully applied to a Rh-catalyzed hydroformylation of various symmetrical and unsymmetrical alkynes to afford corresponding α,β-unsaturated aldehyde products in good to excellent yields (up to 97% yield). Excellent chemo- and regioselectivities and high activities (up to 20 000 TON) were achieved. The corresponding α,β-unsaturated aldehyde products can be transformed into many useful and important organic molecules, such as indenamine derivatives and lukianol pyrroles. This great performance makes the hydroformylation of alkynes highly practical with great potential.
- Zhang, Zongpeng,Wang, Qian,Chen, Caiyou,Han, Zhengyu,Dong, Xiu-Qin,Zhang, Xumu
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supporting information
p. 3290 - 3293
(2016/07/13)
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- Novel electron acceptor -donor-acceptor Naphthalene diimide compound and organic electronic device that contains it
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The present invention relates to an organic semiconductor compound used for manufacturing a novel naphthalene diimide derivative compound in which an electron donor compound is inserted between two naphthalene diimides. Also, a compound is manufactured by synthesizing the organic semiconductor compound of the present invention and substituted or unsubstituted thiophene including a naphthalene diimide derivative and sulfur (S) and accordingly shows a low band gap and, therefore an organic electronic device including the same has a high efficiency. Also, the organic semiconductor compound in the present invention has outstanding thermal stability and physical properties as well as a high interaction between molecules and can be accordingly used as organic semiconductor materials with a high electrical property. The organic semiconductor compound in the present invention can be used in various organic electron devices including an organic thin-film transistor.
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Paragraph 0057-0059
(2016/11/24)
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- Evaporable organic semiconductive material and use thereof in an optoelectronic component
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The invention relates to compounds of general formula IIIa and their use in optoelectronic components.
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Page/Page column 43
(2015/10/05)
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- Unexpected rearrangement during the gas-phase dehalogenation approach to benzodithiophenes
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A range of halogenated methylthiophenes undergo dehalogenative condensation upon FVP over magnesium or calcium to give products including benzodithiophenes; in some cases this involves a novel rearrangement by equilibration of alkenylthienyl radicals via thiophene-fused cyclopropylmethyl intermediates. This journal is
- Aitken, R. Alan,Oyewale, Adebayo O.
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p. 19379 - 19381
(2015/04/14)
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- Electronic properties of thienylene vinylene oligomers: Synthesis and theoretical study
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(E)-1,2-bis(2-thienyl)vinylene (TV), (E)-1,2-bis (3-octyl-2-thienyl) vinylene (TOV), (E)-1,2-bis(3-(2-ethylhexyl)-2-thienyl)vinylene (T2EHV), and (E)-1,2-bis-[2,2'-bithienyl] vinylene (BTV) have been synthesized by a combination of formylation reaction and Mc Murry dimerization. UV-Vis spectra of BTV showed the longest wavelength absorption, TOV and T2EHV showed a bathochromic shift to the red compared with TV, due to an increment of delocalization of the conjugated p-system as the result of the weakening of the carbon-carbon double bonds of the thienyl rings due to the substitution of one hydrogen by the alkyl group. Based on optical data, the effect of linear and branched alkyl chain and extension of conjugation length on the electronic properties is discussed. 1H, 13C-NMR, UV-Visible, Fluorescence data are discussed and theoretical DFT and TD-DFT calculations of ground state and excited states have been also considered in the analysis and explanation of results. Springer Science+Business Media, LLC 2012.
- Neculqueo,Rojas Fuentes,Lopez,Matute,Vasquez,Martinez
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p. 1751 - 1760
(2013/03/14)
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- Identification and quantification of defect structures in poly(2,5-thienylene vinylene) derivatives prepared via the dithiocarbamate precursor route by means of NMR spectroscopy on 13C-labeled polymers
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During the past decades several synthetic routes toward the low band gap polymer poly(2,5-thienylene vinylene) (PTV) and derivatives have been studied. This study describes an extensive NMR characterization of 13C-labeled 3-octyl-PTV and its precursor polymer prepared via the dithiocarbamate route which is, since stable monomers are available, a promising route toward PTV derivatives. By introducing 13C-labeled vinylene carbons, we were able to characterize these polymers in a quantitative way, taking the end groups and structural polymerization defects, which disturb the conjugated system, into account. Several NMR techniques and the synthesis of model compounds were used to fully assign the proton and carbon chemical shifts. Moreover, the classically used thermal conversion of the precursor toward the conjugated polymer has been compared to a smoother, acid-induced elimination procedure.
- Dilien,Chambon,Cleij,Lutsen,Vanderzande,Adriaensens
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experimental part
p. 4711 - 4720
(2012/05/20)
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- McMurry coupling of aryl aldehydes and imino pinacol coupling mediated by Ti(O-i-Pr)4/Me3SiCl/Mg reagent
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Ti(O-i-Pr)4/Me3SiCl/Mg reagent mediated McMurry coupling of aryl aldehydes to biaryl olefins at near room temperature. This low valent titanium (LVT) reagent also mediated the coupling of aldimines to 1,2-diamines (imino pinacol coupling).
- Okamoto, Sentaro,He, Jing-Qian,Ohno, Chihaya,Oh-iwa, Yuhji,Kawaguchi, Yuhki
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experimental part
p. 387 - 390
(2010/03/03)
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- Electronic structural dependence of the photophysical properties of fluorescent heteroditopic ligands - Implications in designing molecular fluorescent indicators
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Two fluorescent heteroditopic ligands (2a and 2b) for zinc ion were synthesized and studied. The efficiencies of two photophysical processes, intramolecular charge transfer (ICT) and photoinduced electron transfer (PET), determine the magnitudes of emission bathochromic shift and enhancement, respectively, when a heteroditopic ligand forms mono- or dizinc complexes. The electron-rich 2b is characterized by a high degree of ICT in the excited state with little propensity for PET, which is manifested in a large bathochromic shift of emission upon Zn2+ coordination without enhancement in fluorescence quantum yield. The electron-poor 2a displays the opposite photophysical consequence where Zn2+ binding results in greatly enhanced emission without significant spectral shift. The electronic structural effects on the relative efficiencies of ICT and PET in 2a and 2b as well as the impact of Zn2+-coordination are probed using experimental and computational approaches. This study reveals that the delicate balance between various photophysical pathways (e.g. ICT and PET) engineered in a heteroditopic ligand is sensitively dependent on the electronic structure of the ligand, i.e. whether the fluorophore is electron-rich or poor, whether it possesses a donor-acceptor type of structure, and where the metal binding occurs.
- Younes, Ali H.,Zhang, Lu,Clark, Ronald J.,Davidson, Michael W.,Zhu, Lei
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experimental part
p. 5431 - 5441
(2011/01/12)
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- Thiazole-based semiconductor compound and organic thin film transistor using the same
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Provided are an organic semiconductor compound using thiazole, and an organic thin film transistor having an organic semiconductor layer formed of the organic semiconductor compound using thiazole. The novel organic semiconductor compound including thiazole has liquid crystallinity and excellent thermal stability, and thus is provided to form an organic semiconductor layer in the organic thin film transistor. To this end, a silicon oxide layer is formed on a silicon substrate, and an organic semiconductor layer including thiazole is formed on the silicon oxide layer. In addition, source and drain electrodes are formed on both edge portions of the organic semiconductor layer. The organic thin film transistor using the organic semiconductor layer has an improved on/off ratio and excellent thermal stability. Also, a solution process can be applied in its manufacture.
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Page/Page column 5-6
(2009/06/27)
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- Effect of base on alkyltriphenylphosphonium salts in polar aprotic solvents
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When arylmethyl phosphonium salts are treated with a base (e.g., t-BuOK or NaH) they homocouple to form symmetric 1,2-diarylethenes. In some cases, dilution and (or) use of excess base lead to very high yields of the product. This reaction is solvent sensitive: the reaction occurs only when polar aprotic solvents such as acetonitrile or DMSO are used. Other alkyl phosphonium salts (e.g., ethoxycarbonylmethyltriphenylphosphonium bromide and n- butyltriphenylphosphonium bromide) form a ylid (when an α-carbonyl group is present) or lose a phenyl group to form alkyldiphenylphosphine oxides when treated with the base. Mechanistic investigation of the homocoupling reaction indicates that the reaction proceeds through a ylid that acts as a nucleophile on an unreacted phosphonium salt. The resulting adduct undergoes elimination to form the observed product. The EIZ ratio seems to depend on the amount of the base used and the phosphonium salt involved.
- Ngwendson, Julius N.,Schultze, Cassandra M.,Bollinger, Jordan W.,Banerjee, Anamitro
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p. 668 - 675
(2008/09/21)
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- A convenient synthesis of symmetric 1,2-diarylethenes from arylmethyl phosphonium salts
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Symmetric ethenyldithiophenes are important intermediates for synthesis of photochromic materials and organic conductors. When acetonitrile is used as a solvent, 3-methylthiophenylphosphonium salts form symmetric ethenyldithiophenes in the presence of a strong base (e.g., NaH, tBuOK) in moderate to high yields. This homocoupling reaction is faster than a Wittig reaction with aromatic ketones in acetonitrile. Our study shows that the presence of polar aprotic solvents promotes the homocoupling reaction.
- Ngwendson, Julius N.,Atemnkeng, Walters N.,Schultze, Cassandra M.,Banerjee, Anamitro
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p. 4085 - 4088
(2007/10/03)
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- Selective synthesis of 1-aryl-2-ferrocenylethylene by cross-metathesis
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Novel synthesis of π-conjugated molecules by cross-metathesis reaction of vinylferrocene with a series of vinylarenes was investigated with a molybdenum-based Schrock catalyst (CHCMe2Ph)Mo(N-2,6-i-Pr2C6H3)[OCMe(C F3)2]2. The cross-metathesis reactions occurred successfully and the cross-metathesis product, i.e., heterodimers, were readily obtained selectively, together with only small amounts of the corresponding self-dimers.
- Yasuda, Tomohiro,Abe, Jiro,Iyoda, Tomokazu,Kawai, Tadashi
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p. 812 - 813
(2007/10/03)
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- Thiaheterohelicenes 1. Synthesis of unsubstituted thia[5]-, [9]- and [13]heterohelicenes
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The unsubstituted thiaheterohelicenes, 5,8-dithia[5]helicene, 1, 5,8,11,14-tetrathia[9]helicene, 2, and 5,8,11,14,17,20-hexathia[13]helicene, 3, have been prepared. The key reaction was the oxidative photolysis of 1,2-diaryl-substituted ethenes which were prepared by Wittig-Horner or McMurry reactions. Acta Chemica Scandinavica 1996.
- Larsen, Jan,Bechgaard, Klaus
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- PREPARATION OF A SERIES OF OLIGOVINYLENES
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Preparation of a series of oligovinylenes (3) is reported.Compounds containing an even number of thiophene rings were synthesised by the carbonyl coupling of thiphenecarbaldehydes with as low-valent titanium reagent and those carrying an odd number of thiophene rings by the copuling of thiophenecarbaldehydes with Wittig-Horner (Witrtig) reagents.Uv-vis spectral feature of these compounds is also reported.
- Nakayama, Juzo,Fujimori, Toru
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p. 991 - 1002
(2007/10/02)
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- REACTIVITY OF HETEROAROMATIC ALDEHYDES WITH LOW VALENT TITANIUM
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Behaviour of various aromatic heterocycles under dicarbonylic coupling with low valent titanium was studied.The results showed that the electron donating properties of the ring affect the degree of oxidation of the coupled compound.
- Castedo, Luis,Cid, M. Magdalena,Dominguez, Rosa,Seijas, Julio A.,Villaverde, M. Carmen
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p. 1271 - 1274
(2007/10/02)
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- THERMOLYSIS OF SODIUM SALTS OF TOSYLHYDRAZONES OF SOME HETEROCYCLIC ALDEHYDES IN THE PRESENCE OF SILVER CHROMATE: 1,3 NC MIGRATION OF TOSYL GROUP
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The thermal decompositions of sodium salts of tosylhydrazones of furfural, thiophene-2-aldehyde, 1-methylpyrrole-2-aldehyde, and pyridine-2-aldehyde in the presence of silver chromate gave 2-furyl(p-toluenesulfonyl)methane, thiophene-2-(p-toluenesulfonyl)methane, 1-methylpyrrole-2-(p-toluenesulfonyl)methane, and pyridine-2-(p-toluenesulfonyl)methane, respectively, via 1,3 NC migration of tosyl group.The same type of reactions with sodium salts of tosylhydrazones of thiophene-3-aldehyde, pyridine-3-aldehyde, and pyridine-4-aldehyde also afforded the corresponding p-toluenesulfonylmethanes but the yields were slightly lower comparing to the above cases.
- Saito, Katsuhiro,Ishihara, Hiraku
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p. 1891 - 1898
(2007/10/02)
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- PREPARATION OF (E)-1,2-BIS-(2,2'-BITHIOPHENE-5-YL)ETHYLENE AND (E)-1,2-BIS(2,2':5',2"-TERTHIOPHENE-5-YL)ETHYLENE
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(E)-1,2-bis(2,2'-bithiophene-5-yl)ethylene and (E)-1,2-bis(2,2':5,2"-terthiophene-5-yl)ethylene were synthesized by reductive coupling reaction of 2,2'-bithiophene-5-carbaldehyde and 2,2':5'2"-terthiophene-5-carbaldehyde, respectively, using a low-valent titanium reagent prepared from titanium(IV) chloride and zinc powder in tetrahydrofuran.
- Nakayama, Juzo,Murabayashi, Shigeru,Hoshino, Masamatsu
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p. 2639 - 2643
(2007/10/02)
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- Preparation de dithienyl-2-ethene-1,2, de dithienyl-2-pyrimidine-2,4 et de dithienyl-2-pyridazine-3,6
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La condensation du reactif de Grignard du bromo-2-thiophene avec les derives bihalogenes, tels que le dichloro-1,2-ethene (Z), la dichloro-2,4-pyrimidine et la dichloro-3,6-pyridazine, en presence de catalyseur a base de metal de transition permet d'obtenir, en une seule etape, des derives polycycliques, comportant deux noyaux thiophenes.
- Montheard, Jean-Pierre,Dubois, Jean-Claude
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p. 719 - 720
(2007/10/02)
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- RHODIUM ION CATALYZED DECOMPOSITION OF ARYLDIAZOALKANES
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Aryldiazomethanes are converted by rhodium(II)acetate and iodorhodium(III) tetraphenylporphyrin to cis- rather than trans-1,2-diarylethylenes.Secondary aryldiazoalkanes react with rhodium(II) acetate to give azines.
- Shankar, B.K. Ravi,Shechter, Harold
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p. 2277 - 2280
(2007/10/02)
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